Not pretending to have all the answers, I do have some ideas. For people like Jimmy Buffet, there was never an agenda. He simply did what he wanted to do and others loved it. Joseph Campbell, the famous storyteller and myth expert said, "Follow your bliss" and the rest will come. But we don't do that.
We remain frozen, thinking we have to follow a path that we did not necessarily choose. How many of us have had occupations by chance, not by choice? You needed a job to pay the bills, got one and stayed there. It is not that you were fulfilled and appreciated at your job, but it did pay the bills and the "living' happened when you were not at work. That is the opposite of Jimmy. His living happened to be his work which he loved. See the difference?
I have followed my bliss over and over again in life, choosing to be a florist, an interior designer, a private investigator and so on, and now a farmer. Those jobs made me happy and the money did come, not hoards of it as in Jimmy's case, but enough to make ends meet. As a farmer, I have experienced some tough times too and had to go back to work to pay the bills, but I am constantly amazed at how things come to me. I believe it is because I am sitting on my beach and playing my own tune.
For example, today, I picked up Hansa Rugosa rose bushes, big huge well established ones and lovely yellow Potentillas. My daughter said I need a place with roses and I agree, and guess what, I have suddenly acquired roses, LOTS of roses. A neighbour did not want the bushes because they prefer lawn to shrubs and it was my good fortune to speak up for them and be given them. I have spent all morning picking them up in 6 different truckloads, but fortunately they are only 5 miles from my place and the man had dug them out with a little machine he had at his place.
Now, I have to go plant all that I reaped. The work will take me all through this day and possibly the next and it is hard work, though I will use the skid steer to dig the holes and cover the plants. I am full of gratitude for this gift.
When we are doing what we love, the benefits begin to unfold in mysterious ways. This is synchronicity, the beauty of a wish coming true, such as my lovely rose bushes. When we are doing what we despise, the joy of life is sapped from us. I know what it is like to be stuck in a job that is secure when there are mouths to feed and bills to pay, but at least consider working towards following your bliss. It is so freeing and so fulfilling and so gratifying. And then we can all be Jimmy's sitting on our "beaches" singing our songs while the money pours in. That is the theory, anyhow. Are you in?